$170 Find Cheap Flights from Hawaii to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 2/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$360
Southwest
Thu 2/26Thu 3/5
HNL - MDW • 1 stop
Cheapest non-stop
$419
Typical prices: $716-$1,708
United Airlines
Wed 2/25Wed 3/4
HNL - ORD • Non-stop
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Hawaii to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hawaii to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hawaii to Chicago

Thu, Feb 26 - Thu, Mar 5
Southwest Logo
9:55 pm - 6:20 pm
HNL
-
MDW
16h 25m
1 stop
Southwest Logo
9:30 pm - 11:00 am
MDW
-
HNL
17h 30m
1 stop
$360Southwest
Thu, Feb 26 - Thu, Mar 5
Southwest Logo
9:55 pm - 1:40 pm
HNL
-
MDW
11h 45m
2 stops
Southwest Logo
8:50 am - 10:10 pm
MDW
-
HNL
17h 20m
1 stop
$366Southwest
Wed, Feb 18 - Tue, Feb 24
United Airlines Logo
10:55 pm - 1:14 pm
HNL
-
ORD
10h 19m
1 stop
United Airlines Logo
9:30 am - 2:54 pm
ORD
-
HNL
9h 24mnonstop
$372United Airlines
Thu, Feb 26 - Thu, Mar 5
United Airlines Logo
12:35 pm - 5:03 am
HNL
-
ORD
12h 28m
1 stop
United Airlines Logo
9:40 am - 3:04 pm
ORD
-
HNL
9h 24mnonstop
$381United Airlines
Thu, Feb 26 - Thu, Mar 5
Multiple Airlines Logo
8:11 am - 11:59 pm
HNL
-
ORD
11h 48m
1 stop
Multiple Airlines Logo
3:07 pm - 10:58 am
ORD
-
HNL
23h 51m
2 stops
$408Multiple Airlines
Thu, Apr 30 - Wed, May 6
Alaska Airlines Logo
7:00 am - 11:59 pm
HNL
-
ORD
11h 59m
1 stop
Alaska Airlines Logo
3:52 pm - 5:32 pm
ORD
-
HNL
30h 40m
1 stop
$412Alaska Airlines
Thu, Apr 30 - Wed, May 6
Multiple Airlines Logo
7:00 am - 11:59 pm
HNL
-
ORD
11h 59m
1 stop
Multiple Airlines Logo
3:52 pm - 8:26 pm
ORD
-
HNL
33h 34m
1 stop
$421Multiple Airlines
Wed, Feb 18 - Sun, Feb 22
American Airlines Logo
10:11 pm - 12:31 pm
KOA
-
ORD
10h 20m
1 stop
American Airlines Logo
9:25 am - 6:59 pm
ORD
-
KOA
13h 34m
1 stop
$422American Airlines
Wed, Feb 18 - Sun, Feb 22
Alaska Airlines Logo
11:54 pm - 2:58 pm
OGG
-
ORD
11h 04m
1 stop
Alaska Airlines Logo
8:20 am - 2:52 pm
ORD
-
OGG
34h 32m
1 stop
$432Alaska Airlines
Tue, Feb 17 - Thu, Feb 26
American Airlines Logo
10:11 pm - 12:31 pm
KOA
-
ORD
10h 20m
1 stop
American Airlines Logo
11:31 am - 6:59 pm
ORD
-
KOA
11h 28m
1 stop
$445American Airlines
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$170
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Honolulu to Chicago O'Hare Airport

FAQs for booking flights from Hawaii to Chicago

  • How does KAYAK find such low prices on flights from Hawaii to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hawaii to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Hawaii

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicagofrom $2,717
Business Class flights to Chicagofrom $2,872
Premium Economy Class flights to Chicagofrom $694
Economy Class flights to Chicagofrom $334